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3577-01-3

Basic Information
CAS No.: 3577-01-3
Name: cefaloglycin
Article Data: 4
Molecular Structure:
Molecular Structure of 3577-01-3 (cefaloglycin)
Formula: C18H19 N3 O6 S
Molecular Weight: 405.431
Synonyms: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-[(acetyloxy)methyl]-7-[(aminophenylacetyl)amino]-8-oxo-, [6R-[6a,7b(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[[(2R)-aminophenylacetyl]amino]-8-oxo-, (6R,7R)- (9CI);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-, acetate (ester), D-(8CI); 7-(2-D-a-Aminophenylacetamido)cephalosporanicacid; Cefaloglycin; Cefaloglycine; Cephaloglycin; Cephaloglycine;D-(-)-Cephaloglycin; D-Cephaloglycine; Kafocin; Kefglycin; Lilly 39435
Density: 1.52g/cm3
Melting Point: 236.5°C (rough estimate)
Boiling Point: 761.8°C at 760 mmHg
Flash Point: 414.5°C
Solubility: 10.5g/L(25 oC)
Hazard Symbols: Xn
Risk Codes: 42/43
Safety: Moderately toxic by subcutaneous and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.
PSA: 164.33000
LogP: 1.01720
Synthetic route
7765-60-8

(6R)-3-acetoxymethyl-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

3577-01-3

cephaloglycin

Conditions
ConditionsYield
(i) CF3CO2H, (ii) ion exchange resin - form>; Multistep reaction;
24461-61-8

(R)-Phenylglycine methyl ester

957-68-6

7-Aminocephalosporanic acid

3577-01-3

cephaloglycin

Conditions
ConditionsYield
at 30℃; for 3h; Pseudomonas melanogenum KY 3987 and KY 8540; Yield given;
19883-41-1

D-phenylglycine methyl ester hydrochloride

957-68-6

7-Aminocephalosporanic acid

3577-01-3

cephaloglycin

Conditions
ConditionsYield
With potassium phosphate; Pseudomonas melanogenum KY 8541 at 30℃; pH=6.5;
33125-05-2

Boc-D-Phg-OH

3577-01-3

cephaloglycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) Et3N, (ii) iBuOCOCl, (iii) /BRN= 5406532/
2: (i) CF3CO2H, (ii) ion exchange resin - form>
View Scheme
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

3577-01-3

cephaloglycin

7β-[D-2-(Chromone-3-carboxamido)-2-phenylacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid

Conditions
ConditionsYield
In dichloromethane; ethyl acetate55%
3577-01-3

cephaloglycin

4704-60-3

cephalosporanic acid

Conditions
ConditionsYield
26%
triethylamine salt of cephaloglycine

triethylamine salt of cephaloglycine

42835-54-1

1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

3577-01-3

cephaloglycin

543-27-1

isobutyl chloroformate

71-36-3

butan-1-ol

sodium 2-ethylhexanoic acid

73253-21-1, 115404-31-4

(6R)-3-acetoxymethyl-8-oxo-7t-[(R)-2-(1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonylamino)-2-phenyl-acetylamino]-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
With magnesium sulfate; triethylamine In N-methyl-acetamide; diethyl ether; dichloromethane; water
triethylamine salt of cephaloglycine

triethylamine salt of cephaloglycine

42835-34-7

5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid

3577-01-3

cephaloglycin

543-27-1

isobutyl chloroformate

71-36-3

butan-1-ol

sodium 2-ethylhexanoic acid

73253-22-2

(6R)-3-acetoxymethyl-7t-[(R)-2-((Ξ)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonylamino)-2-phenyl-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
With magnesium sulfate; triethylamine In N-methyl-acetamide; diethyl ether; water
triethylamine salt of cephaloglycine

triethylamine salt of cephaloglycine

3577-01-3

cephaloglycin

73004-70-3

8-(4-formyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

543-27-1

isobutyl chloroformate

71-36-3

butan-1-ol

sodium 2-ethylhexanoic acid

73253-23-3

(6R)-3-acetoxymethyl-7t-{(R)-2-[8-(4-formyl-piperazin-1-yl)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonylamino]-2-phenyl-acetylamino}-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions
ConditionsYield
With magnesium sulfate; triethylamine In N-methyl-acetamide; diethyl ether; water
60-29-7

diethyl ether

3577-01-3

cephaloglycin

sodium 2-ethylhexanoic acid

N-[6-[4-[N-Methyl-5-oxo-L-prolylamino]phenyl]-1,2-dihydro-2-oxo-nicotinyl]-7-[D-2-amino-2-phenylacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid

Conditions
ConditionsYield
With dimethyl sulfoxide In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl acetamide; ethyl acetate
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Chemistry

Chemistry informtion about Cefaloglycin (CAS NO.3577-01-3) is:
IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-Amino-2-Phenylacetyl]Amino]-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid
Synonyms: Cefaloglycin ; Cephaloglycin ; (6r,7r)-7-[(R)-2-Amino-2-Phenylacetylamino]-3-(Acetoxymethyl)-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid ; Cephaloglycin(Anhydrous) ; Kafocin ; Kefglycin ; Lilly-39435
MF: C18H19N3O6S
MW: 0
EINECS: 222-696-7 
Density: 1.52 g/cm3
Flash Point: 414.5 °C
Boiling Point: 761.8 °C at 760 mmHg
Vapour Pressure: 2.14E-24 mmHg at 25°C 
Enthalpy of Vaporization: 116.41 kJ/mol
Following is the molecular structure of Cefaloglycin (CAS NO.3577-01-3) is:

Production

Preparation Products is Cefpimizole .

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1030mg/kg (1030mg/kg) kidney, ureter, and bladder: "changes in tubules (including acute renal failure, acute tubular necrosis)" Chemotherapy Vol. 18, Pg. 22, 1970.
mouse LD50 oral > 10gm/kg (10000mg/kg) liver: other changes Chemotherapy Vol. 18, Pg. 22, 1970.
mouse LD50 subcutaneous 3700mg/kg (3700mg/kg) kidney, ureter, and bladder: "changes in tubules (including acute renal failure, acute tubular necrosis)" Chemotherapy Vol. 18, Pg. 22, 1970.
rat LD50 intraperitoneal 1300mg/kg (1300mg/kg) kidney, ureter, and bladder: "changes in tubules (including acute renal failure, acute tubular necrosis)" Chemotherapy Vol. 18, Pg. 22, 1970.
rat LD50 oral > 10gm/kg (10000mg/kg) liver: other changes Chemotherapy Vol. 18, Pg. 22, 1970.
rat LD50 subcutaneous 2800mg/kg (2800mg/kg) kidney, ureter, and bladder: "changes in tubules (including acute renal failure, acute tubular necrosis)" Chemotherapy Vol. 18, Pg. 22, 1970.

Safety Profile

Moderately toxic by subcutaneous and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.

Specification

 Cefaloglycin (CAS NO.3577-01-3) is a first generation cephalosporin antibiotic.